Thuyen, David
Thuyen, David>>>
The starting material, 1,9-nonanediol found in signmaaldrich.com, was treated with HBr as a reagent and resulted in
1-Bromo-1-tetradecyne. One of the -OH groups was substituted with Br.The molecule was then treated with dihydropyran, the alkene in the ring broke to form a bond on to the oxygen of the 1-Bromo-1-tetradecyne, and Br acted as a leaving group with an alkyne come in its place. Then the molecule was reacted through Jones Oxidation to result in a carboxylic acid group on the end of the molecule. In the second to last step the molecule was treated to with alcohol and H-O-CH3. Finally in a Base and SuBr the two long chains were brought together and produced pentacosa-10,12-diynoic acid.
References: http://www.chemspider.com/Search.aspx?q=C5H8O&rid=046a13cb-9c31-492c-b0e4-73ed5322033e http://www.organic-chemistry.org/namedreactions/jones-oxidation.shtm
Wade, L.G. Organic Chemistry. 7th. Prentice Hall, 2009. This looks like a workable synthesis. You just need to finish the description with references. Bruce Bondurant
Dionne Milan, Ashleybeth Martinez, Lanny Lantigua
Dionne Mila Ashleybeth Martinez,Lanny Lantigua
This is a nice synthesis and description. You just need to add references and you are done. Bruce Bondurant Reference: Notes taken at class, and reference paper from shared files
Thuyen, David
Thuyen, David>>>
The starting material, 1,9-nonanediol found in signmaaldrich.com, was treated with HBr as a reagent and resulted in
1-Bromo-1-tetradecyne. One of the -OH groups was substituted with Br.The molecule was then treated with dihydropyran, the alkene in the ring broke to form a bond on to the oxygen of the 1-Bromo-1-tetradecyne, and Br acted as a leaving group with an alkyne come in its place. Then the molecule was reacted through Jones Oxidation to result in a carboxylic acid group on the end of the molecule. In the second to last step the molecule was treated to with alcohol and H-O-CH3. Finally in a Base and SuBr the two long chains were brought together and produced pentacosa-10,12-diynoic acid.
References:
http://www.chemspider.com/Search.aspx?q=C5H8O&rid=046a13cb-9c31-492c-b0e4-73ed5322033e
http://www.organic-chemistry.org/namedreactions/jones-oxidation.shtm
Wade, L.G. Organic Chemistry. 7th. Prentice Hall, 2009.
This looks like a workable synthesis. You just need to finish the description with references.
Bruce Bondurant
This is a nice synthesis and description. You just need to add references and you are done.
Bruce Bondurant
Reference: Notes taken at class, and reference paper from shared files